In today’s fast-evolving business landscape, leaders often find themselves at critical turning points—moments when the familiar terrain of their career shifts beneath their feet, prompting deep reflection on their role and future. This was the case for Maggie, a seasoned leader who has grown alongside her company from its startup roots to a more mature, scaling organization. As her company enters a new phase characterized by different expectations and leadership, Maggie faces uncertainty about where she fits and how to continue adding value. Executive coach Muriel Wilkins steps in to guide Maggie through this complex transition, helping her define her worth, navigate organizational change, and prepare for the next chapter of her professional journey.
**A Journey from Startup Generalist to Organizational Uncertainty**
Maggie’s story begins with a rare professional trajectory: she has spent most of her career at one company, starting with a small startup and evolving alongside it through multiple growth phases. Over the years, she has taken on new challenges, expanded her skill set, and climbed the corporate ladder—often by volunteering for unclaimed responsibilities and tackling problems head-on. This hands-on, roll-up-your-sleeves approach has made her invaluable during the company’s early and middle stages. However, as the company grows larger and more complex, Maggie senses a shift. The “all-hands-on-deck” culture is giving way to a structure that values specialization, clear role definitions, and defined leadership scopes.
Maggie articulates a key internal question: “Am I the person this organization needs long term?” She recognizes that with new leadership and evolving expectations, the pathways for advancement and contribution look very different than before. Unlike earlier in her career, where opportunities came in the form of undefined challenges she could claim, now roles are more guarded, expectations are more precise, and proving her value requires navigating new dynamics without the same clarity or feedback she once had.
**The Challenge of Navigating Ambiguity and Redefining Value**
Muriel helps Maggie unpack the experience of feeling caught on a “precipice” — an uncertain moment right before a major organizational transformation. Maggie admits that this is the first time she’s felt unsure about her fit within the company, largely because new leaders are still learning about the business and shifting strategies frequently. This “discovery phase” means that the company itself is in flux, and by extension, so is Maggie’s role.
A significant part of Maggie’s struggle is the absence of consistent feedback from new leadership. Unlike before, when her contributions were visible and directly tied to results that leadership recognized, now she finds herself working hard to prove her worth without clear confirmation that she’s on the right path. This lack of feedback creates a vacuum of uncertainty, leading Maggie to question her abilities and long-term place in the organization.
Muriel points out that Maggie is grappling with two distinct but intertwined challenges: managing the present uncertainty of the “precipice phase” and envisioning what her future role might look like in the new organizational era. She encourages Maggie to first focus on what she can control—her day-to-day actions and short-term goals—to build a stable foundation before trying to solve the bigger unknowns.
**Building Strong Footing in the Present**
To regain a sense of control and confidence, Muriel suggests Maggie establish clear, short-term measures of success. This could mean setting weekly goals that reflect the current demands of her role and tracking progress against them. By focusing on tangible, immediate achievements rather than nebulous future expectations, Maggie can maintain a sense of grounding and accomplishment even as the larger organizational picture remains unclear.
Maggie acknowledges that she has a tendency to think big-picture and operate as the “tip of the spear,” but in this moment of change, narrowing her focus to manageable, measurable tasks feels like a crucial shift. This approach not only builds momentum but also creates a record of impact that Maggie can point to as she seeks clarity from leadership.
**Exploring New Definitions of Leadership Value**
A core insight from the conversation centers on how Maggie has historically defined her value: by taking on more and more responsibilities across a wide range of areas. In a startup environment, this generalist approach is often essential. But as companies scale, leadership roles tend to specialize, requiring deep expertise in specific domains rather than broad involvement.
Muriel challenges Maggie to consider alternative ways of defining her value that don’t rely on doing “everything.” This means identifying areas where Maggie’s unique skills and experiences can make the most